


The New Rocket Plan (Request)

by CTFMeister



Category: Pocket Monsters | Pokemon (Anime)
Genre: Gender Bender, Male to Female, Mind Change, Transformation
Language: English
Status: Completed
Published: 2018-07-20
Updated: 2018-07-20
Packaged: 2019-06-13 06:16:33
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,683
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15358074
Author URL: https://archiveofourown.org/users/CTFMeister/pseuds/CTFMeister
Summary: Jessie has received new mission, along with new Pokemon that will help her finally obtain victory over Ash. And to the victor goes the spoils.





	The New Rocket Plan (Request)

Jessie walked along the thick forest with a confident gait. Behind her, James and Meowth waded by wearily, lacking the determination and energy of their partner-in-crime. Their target was the same as always, Ash Ketchum and his darned Pikachu. Although this time, their goal was a bit different…

“I just don’t get it.” Spoke up Meowth, breaking the silence. “What’s da plan to beat the twerp this time?”

“Hmm.” Jessie smirked. “We’re going to challenge him to a Pokemon battle and win.”

“That can’t work, right?” James interjected. “Even if we beat him in a battle and win-” A task James thought was not possible. “It’s not like he’s going to surrender his Pokemon willingly.”

Jessie merely grinned smugly. Yes, if she was in the dark about their current situation she too would have expressed doubt. But this was not the case. As the most level-headed member of the team, she was the only one to receive some confidential information about her new task from the boss. Yes, they were to confront Ash once more, but this time, things were going to go different.

Clutching her Pokeballs tightly, Jessie felt a surge of power course through her. These were the source of her confidence. Three Pokemon, gifted to her by Giovanni himself, that were more powerful than any other Pokemon she’d seen before. And she had seen a LOT of Pokemon before. Even Gym Leaders and Champions would be crushed under their might. With these monsters there was no way they could be defeated, and Jessie was ready to face the twerp. Her body shivered with excitement as they approached Ash’s training site.

 

“Pikachu use Thunderbolt!” Ash yelled at his Pokemon.

Pikachu happily complied, shooting out a pole of electricity towards a nearby rock and pulverizing it entirely, smoke rising up from the hit. The dust slowly settled down onto the ground, making Ash grin widely. A hole was produced in the stone, indicative of Pikachu’s strength. 

He wiped some sweat from his brow. Things were really going well today. He’d set out early morning towards this isolated clearing to practice with Pikachu. Though early morning practice was always rough, it felt great to see the slow improvement it had on his Pokemon.

Pikachu looked at Ash proudly with an expectant smile. Ash giggled. “Good job buddy. With this, we’ll surely beat the next Gym Leader!”

Ash ducked down and began patting Pikachu’s head, who gladly received his trainer’s affection and praise. That was, until he detected something amiss. Pikachu’s expression soured, as he got on all fours and began growling towards the forest. Noticing his Pokemon’s concern, Ash turned towards the direction he was looking, to find no one else but Team Rocket themselves.

“Team Rocket!” Ash yelled angrily. Standing up straight, he fearlessly faced his foe. “What are you doing here?”

Jessie grinned at the sight of the angered twerp and his twerp rat. The two of them stood their ground, postures full of confidence and fully unaware of what was going to happen to them next.

“Oh my… Can’t a couple of trainers take a walk through the forest?” Jessie asked coyly.

“No way.” Ash responded. “You guys are definitely up to no good.”

“Very well then, how about we settle this with a Pokemon battle?” Jessie gave a villainous smirk, doing her best to contain her inner excitement.

Ash and Pikachu looked at each other, then suddenly burst out into laughter. “Really?” Ash asked incredulously. 

“Of course~” Jessie answered boldly. “Unless you’re scared…”

Not one to turn down a fight, he grabbed the bill of his hat and turned it backwards, his look becoming completely serious. “Alright. If you want to do this… Let’s fight.”

“Very well!” Jessie said joyously. “Prepare for trouble, twerp!”

“And make it double-”

“James…” Jessie said interrupting him. She stared daggers towards her partner, making him promptly shut up.

Then, as the man fell quiet once more, her serene attitude returned. She grabbed the three Pokeballs on her belt and threw them. “Gardevoir! Lopunny! Lilligant! Go!”

The Pokeballs flew up in the air, unleashing bright red lights that generated the three: Gardevoir, Lopunny and Lilligant. As the trio reached the ground and focused on Ash, Pikachu began feeling shudders go down his spine. These Pokemon… They were different from anything he’d fought before. 

Their eyes were cold and uncaring, their posture static and unnatural. They stood menacingly, more like robots than Pokemon, while waiting for orders from the trainer. These didn’t feel like Pokemon, they felt like demons. However, regardless of how threatening these creatures seemed, Pikachu was determined to do his best to protect his trainer. He stepped forward bravely ready to enter the fight.

Seeing the courage of his friend, Ash felt a surge of confidence in their abilities. “Alright, Pikachu! Let’s do it, I choose you!”

Pikachu jumped up and in front of Ash, standing his ground as he charged electricity with his cheeks.

Jessie gave an unimpressed look. “Gardevoir, please take care of that bothersome rodent. Oh, but make sure not to kill him, just hurt him very, very badly~”

Gardevoir stepped up to the plate, bearing the same blank expression. 

“Alright!” Meowth stepped onto the middle of the field, holding his paw up in the air. “Let the battle start in… Three! Two! One! GO!” 

Meowth slung his paw down and quickly jumped out of the field, as Pikachu began speeding towards Gardevoir with a defiant look. He zipped left and right, approaching his target at menacing speeds so fast that it was hard to keep up with him. Though this show of force had no effect on Gardevoir nor its trainer, as they remained as emotionless as they were before.

“Pikachu use Iron Tail!” Ash yelled out to his partner.

Pikachu jumped up in the hair, his tail glowing a shining silver as he began speeding down towards Gardevoir. However, as Pikachu rained down onto his target, Gardevoir remained perfectly still, staring at him with an uninterested, fearless expression. That is, until eventually Pikachu crashed down onto the ground, sending a cloud of dirt up un the air.

Ash shook his fist in joy at the sight, happy to have taken out the Gardevoir so quickly. Though as soon as the cloud of smoke disappeared, both him and his Pokemon soon found that they had missed their target. There was a large hole in the ground where Gardevoir was standing, but Gardevoir herself was nowhere to be seen.

Suddenly, Gardevoir reappeared behind Pikachu, looking as if nothing had happened. Jessie smirked, both Ash and Pikachu staring at the Psychic Pokemon in shock. 

“Ok Gardevoir! Use Psychic!” Jessie yelled out with glee.

Gardevoir gave a meek nod, then lifted her hand towards Pikachu. A violet aura encased the electric mouse, making him completely unable to move. Gathering up all his strength, Pikachu did his best to try to struggle out of the psychic field, shocking the air around him in an attempt to set himself free. But Gardevoir’s grasp was too strong.

The psychic Pokemon lifted up her hand, causing Pikachu to float up in the air. Then, with a swift motion, she threw her hands towards Ash, sending Pikachu crashing away in the same direction. The mouse flew by at incredible speeds, only stopping as he collided head-first against a large boulder behind his trainer, a cloud of debris and dust rising up in the air.

Ash stood there watching in astonishment. While the debris began to clear, he quickly ran up to his friend to check if he was ok. Though the hit had looked massive, Ash had hoped that maybe by some miracle Pikachu would be able to take it. Unfortunately, this was not the case as his small compadre laid fainted on the ground.

His little partner had been decimated in a single blow… And by Team Rocket no less… How could that be possible. No, Ash wouldn’t let this end this way. He’d never lost to Team Rocket before, and today was no different. He still had some more Pokemon and the will to fight, so he would definitely get payback for what they did to his best friend.

Ash stepped back up to the plate with a determined look on his face. “Alright, let’s get serious then-”

He reached to grab one his Pokeballs when suddenly-

“Enough!” Jessie yelled out in annoyance. “I already beat up that stupid rat of yours and I don’t think any of your other vermin will fare any better. Besides, I’m getting tired of this battling stuff, so why don’t we just cut to the chase? Gardevoir?”

Ash was about to give an impassioned reply about the sacredness of Pokemon battles, when he found he was suddenly unable to speak. In fact, he was completely unable to do anything at all. He tried to reach down and grab a Pokeball from his belt, but he was completely frozen. Ash focused his gaze forward. The same pinkish aura that was covering Pikachu was now covering him!

“Alright girls~” Jessie said as she approached Ash with a cocky step. “You know what to do.”

All of Jessie’s three Pokemon nodded meekly, and they began approaching Ash slowly. Fear crept into the boy’s mind, trapped within the paws of Team Rocket, here in the woods where no one would find him. What were they going to do to him?

From his peripheral vision, Ash saw his clothes being surrounded by more Psychic aura. They began to pull away from his body, stretching and straining as the separation force grew stronger. Until- SNAP! His clothes were entirely ripped from his body, leaving the boy completely naked. Ash tried to reflexively cover his naked bits, but again was unable to move thanks to his current constraints.

Gardevoir adjusted Ash’s posture to something more manageable, straightening out his extremities to leave his entire body exposed. Ash gave a raging look. He couldn’t let this humiliation happen to him. He began to struggle as hard as he could away from the energy, though his concentration was broken as he noticed Gardevoir close her eyes to use another move.

All of a sudden, Ash’s entire body was encased within a large purple room that was flowing with Psychic energy. Garevoir opened her eyes and stared directly at Ash with the same blank expression she bore, but this time, Ash felt truly afraid and powerless.

Gardevoir slowly approached the boy and submerged her hands inside the cube. She placed then on his waist, and then began to squeeze them together. Surprisingly, Ash didn’t feel much pressure or pain as she pressed her hands closer, almost as if his body was made of clay and could be molded in whichever way. Ash couldn’t believe it. He didn’t want to. But as Gardevoir released her grip of him and his body retained the shape she had produced he had to accept it. They were sculpting his body into something different!

His stomach area was next. Gardevoir pressed his belly and his back together until the little flab that was there receded to form a fully flat and soft stomach with a thin curvy waist. She then moved down his legs, pulling on his sides to create long curvaceous thighs that would make any girl jealous. 

Grabbing both buttcheeks, she pulled on them lightly, gyrating her arms in circular motions as Ash’s ass expanded outwards, all blemishes faults disappearing to leave nothing but a plentiful round booty. She then knelt down and gripped one of his legs, stretching it into a thick and meaty appendage. Pulling her hands down, all of his hair disappeared to make way for silky smooth soft skin, as they passed around it. This process was then repeated with his other leg, as Ash’s entire lower body was transformed into that of a female.

Everything but one little detail. Gardevoir lifted her hand and took hold of Ash’s flaccid penis. She grabbed it by the head and began pushing him inwards, with the dick slowly but surely following its path, losing inch after inch of length. Its skin was peeled back entirely, and the capped head turned into a conical shape. As Gardevoir’s finger reached Ash’s crotch, his penis was no more, now just a tiny pink nub.

His balls were next. Gardevoir gave his sack a little pull and inertia did all the work for her, with the pouch bouncing back up and receding into his skin, their mass disappearing and the balls floating deep inside him. Soon, nothing but a flat soft piece of skin was left of Ash’s sack. But Gardevoir wasn’t done, she used her hands to pull the skin underneath Ash’s nub apart until a small hole formed, which parted deep inside him to form a fully functional uterus. There, as vaginal fluids leaked from Ash’s new organ, his sexual change was complete.

With Ash’s lower body done, Gardevoir moved on to his upper body. She began by fondling his chest softly, turning his rough rugged chest softer and more feminine. Then she started pulling on his nipples, which caused them to become redder, more sensitive and puffed up. What’s more, as his nipples were pulled his chest were pulled along behind them, the skin of his formerly flat chest stretching out as his pecs were filled with more and more mass. After Gardevoir finally let go, Ash’s new bust pulled backwards, now a coupled of DD-sized breasts that bobbed down from his chest.

Gardevoir followed this up with his arms. She took hold of one of them and pressed her hands together lightly. Then, as she pulled her hands from the shoulder down to his wrist, any hairs and muscle disappeared, his arms turning dainty and feminine, until she reached his hands. She took hold of his hand and massaged it softly, all the roughness transforming into softness as his nails grew and fingers became slender. This process was repeated with his other arm, and Gardevoir moved to his shoulders, where she kneaded them softly to make them slenderer and slanted.

Finally, Gardevoir came to the head. She began with the hair, pulling it down until Ash’s modest haircut was turned into a cascade of flowing black locks. She then proceeded to grab Ash’s throat. The boy struggled a bit, fearing he’d be strangulated. But nothing of the sort happened. Rather, Gardevoir was molding it, so that his vocal chords would be changed to a more feminine tone.

Gardevoir began caressing Ash’s face. She kneaded her hands around it lightly, making sure to eliminate any blemishes and imperfections that might get in the way. She pushed a bit of his nose in, making it a petite and soft addition to his facial structure. She pulled his lips a bit, giving the boy large luscious lips perfect for any variety of sucking that might be needed.

With Ash’s transformation into a sexy voluptuous woman complete, Gardevoir let out a sigh of relief. Her job was done. She dissipated the box Ash was in and released him from he psychic control, making the boy(?) fall down onto his enlarged bum.

“Oww! What did you do to-!” Ash quickly covered his mouth as he heard the new high-pitched voice that left through it.

Though surprised, Ash was still as determined as ever. He wouldn’t let himself be deterred just by this. He was about to stand up and face Jessie when- Fwoop. Lopunny lifted Ash from the ground by the armpits. 

This wasn’t the innocent gesture it seemed to be though as, instead of putting him down, Lopunny grabbed Ash by the waist with one arm and kept him up in the air. Ash looked down at the bunny, only to see she was pulling out what could barely be considered a piece of underwear. That moment, he understood what was next. Of course, he tried to struggle out of her paw, but the dainty Pokemon was sturdier than it looked like.

The panties Lopunny held in her hand were more like three pieces of interconnected pink string that would barely be able to cover a woman’s private area. Through the boy’s squirming, she was able to slide the panties up through his legs until it fit snugly around his crotch.

Next, she pulled out a bright blue tight-fitting miniskirt and slid it up the struggling boy’s legs. They stuck neatly to his thighs, accentuating his new womanly curves and buttocks very tightly. The skirt itself was very comfortable and soft though, with easy access to Ash’s new organ, which was the most important part.

A red-hot pair of high heels then appeared on Lopunny’s paw as Ash began to wonder where this Pokemon was pulling all the clothes from. Slowly and with care, Loppuny slipped Ash’s dainty feet into the shoes, which fit in perfectly as if the heels themselves were custom made.

Then, with the same suddenness with which Lopunny had picked Ash up, she put him back down, making Ash wobble in surprise from his sudden freedom. Lopunny started to walk around him, which gave Ash a sparking thought. If he wanted to escape, the time was now. Though as soon as he tried to lunge forward, he was met with a great issue, he didn’t know how to stand, much less walk, in heels.

So, the boy lost his balance, making him tip forward, then backward, as he began to fall back before Lopunny caught him by the armpits again. Ash gave her a thankful smile, forgetting that it wasn’t an act of kindness by the Pokemon, rather it was merely doing its job. Setting him straight, she continued to dress him up without much care.

The bra was next. Lopunny stretched her hands over Ash’s head, holding a white almost see-through bra and pulled back, bounding Ash’s free flesh mounds inside its fabric. She stretched the cloth back and closed the bra-hook, making his breast’s look tight and compact.

She then held Ash’s arms up, while she slipped a blue tube top down his arms and onto his chest. Ash shook his head, looking down to see the outfit he was just given. The top and skirt were so short and revealing that he still felt naked. Add to that the shoes, he looked like any common street walker!

Ash began to move in an attempt to do something but was pulled back as Lopunny held his hair. The bunny began combing it thoroughly with her hands, which were actually soft and frizzly enough to do a decent job at it. She brushed up and down, getting rid of any craziness, until Ash’s long curly jet black hair was straightened out and shining.

One of Ash’s hands went to the back of his head to feel it. It actually felt really good. His long hair was so soft and silky, like a brand new blanket covering her his head. But once Ash’s attention left his hair, he’d realized the Lopunny was right in front of him, a bunch of makeup utensils in her hands.

Before Ash could even think of protesting, Lopunny used her free hand to grab Ash’s neck. She squeezed it softly enough so that it wouldn’t hurt, but tightly enough so that air was having a hard time getting through his throat. With any possible interruptions prevented, Lopunny began working on Ash’s face.

First up was foundation, to clean up any remaining blemishes Ash’s face had. Next came the concealer and the eyeshadow, Lopunny moving her hand in fast precise motions that looked like and a painter producing his masterpiece. Thick strokes here, thin brushes there, in a few mere seconds Ash’s face was transformed into that of a princess, his features shining as brightly as the sun. Then, the last part. Lopunny pulled a tube of red lipstick and applied it to his lips, giving the sparkle of life, the finishing touch to complete this piece of art.

With her job done, Lopunny let go of Ash’s neck, a sigh of relief escaping her breath. Ash almost fell to the ground as he felt control go back to his legs, somehow able to maintain balance while standing in heels. But as stood up straight, he came face to face with the last member of Jessie’s team.

Standing before him, was Liligant, who just like the other two seemed innocent enough. That’s when it began dancing. With it’s stubby legs, it began moving from side to side, left to right, twirling and swirling around in a dance that was unlike any Ash had ever seen. It was so convoluted, so disorienting, it started making Ash very confused.

Ash’s eyes started to swirl around in his head as his mental faculties were diminished. He found it hard to tell left from right, so he absolutely didn’t notice as Lilligant began releasing a slew of rose pinkish pheromones that traveled through the air. They entered through Ash’s nose and made their way up the feeble boy’s system, as they began rewiring his mind and thoughts.

First to go were his conceptions on his identity. Having big breasts and a vagina, Ash wasn’t a very good name for him. In fact, he wasn’t even a guy! She was a beautiful buxom babe, and Ashley was a name that fit much better. In fact, Ashley like her name so much, that she only talked about herself in the third person.

Then there was her love of Pokemon battling. Savage things such as battling, and fighting weren’t very girly. No, Ashley much preferred thinking about dresses, make-up and guys. All of Ashley’s knowledge about Pokemon fighting was transferred into those subjects, as she forgot type advantages in favor of what colors looked good on her, and all those pesky pokemon trivia turned into info on how to get guy’s attention.

And man did she love boys. All those desires to be a Pokemon master and to catch them all were syphoned into a deep desire to attract men. Lust and sexual information flooded her mind as she began dreaming about sucking big meaty cocks and having her pussy plowed instead of playing with dumb animals.

Soon, the sweet scent began dissipating from the air and Ashley’s consciousness slowly returned. She shook her head. Had something happened to her? She looked at the Lilligant, who was stepping away now that her job was completed and wondered what they had done to her this time.

However, Ashley didn’t have time to think about that. With the three Pokemon having disengaged from her, this was her chance to finally confront Jessie and get her to change her back. With perfect precision, Ashley stomped angrily towards Jessie, a large pout on her face.

“Hey! What have you done to Ashley!” Ashley asked loudly. Though an alarm went off in her head as she heard her name. 

“Wait a second, Ashley’s name isn’t Ashley…” She said with a confused tone. “Ashley is a girl name. Ashley isn’t a girl… ?” Ashley said that but her confidence in the statement was diminishing.

“Oh my dear Ashley…” Jessie said softly as she placed her hands on Ashley’s shoulders. “Of course you’re a girl. I mean, just look at your body. Would a boy have tits as big as this?” Jessie said, grabbing onto one of Ashley’s breasts as a moan came out of the girl’s mouth.

Ashley frowned. Jessie was right. Boys didn’t have big titties, so Ashley couldn’t be a boy. It made sense, but something didn’t feel right…

“Now girl, don’t look so down…” Jessie tried to soother her. “I know what will cheer you right up. How about I find you a big meaty cock?”

Ashley’s eyes lit up like a bright star, the word echoing deep inside her mind. Cock? Why did it sound so appealing? Just thinking about it made her body shiver. Their scent, their look, their taste… God, what Ashley wouldn’t give to get access to some cock right this instant.

As Ashley’s mouth salivated to the thought of dick, Jessie gave a devilish smile. Not to be one to disappoint a beautiful girl, she stepped back to get James, who had been standing and watching the entire scenario in awe. Jessie pulled James towards the hungering girl, though the man felt very unsure about the whole situation.

“Jessie, I don’t know about this.” James expressed in a concerned tone. “This whole deal just feels wrong, you know?”

Stopping in front of Ashley, Jessie stepped behind James, her hands gripping his pants tightly. “Oh come on James. Don’t be such a party pooper and, ENJOY!” She yelled out, as she pulled down on James’ pants, which fell onto the ground along with his underwear to reveal James’ hardened cock.

Ashley’s expression turned into one of pure joy as soon as she caught sight of James’ freed package. Like a wild beast upon seeing its prey, she pounced on top of the man, sending them both tumbling to the ground. The grunt tried to struggle away as well as a man with an penis erect and his pants down could. But it was of no use, Ashley quickly sat on top of him, a hungry look on her face. Without any care, she discarded the panties she was wearing and pressed her wet womanhood against his pole. This was it… The dick she so desperately needed was so close to her… Just a little more and…

With a sopping wet slap, Ashley devoured James’ entire dick with her cunt. Her eyes rolled back, as the two happily cooed out in pleasure. But it wasn’t enough, Ashley needed more. So the girl began to rhythmically move her hips up and down, any and all other worries she had in her mind starting to disappear. Her Pokemon, her goals, the changes to her body, none of them mattered. Now the only thing that mattered, was the delicious dick she was taking into her vagina, and how good it made her feel.

Jessie took a step back to proudly admire her creation. This was it, she’d done it. Not only had she finally defeated the stupid kid that had been ruining her life for so long, she managed to absolutely humiliate him. It felt good to be on the winning side for once, to have completely destroyed this twerp’s life. And she wouldn’t have done it without them.

She turned lovingly towards the pokemon who had made all of this possible. “Good job girls~” She sung happily, as she threw each one of them a delicious pokepuff.

The pokemon looked at the treats in confusion, not having been used to being shown affection after so many years of torture in the rocket labs. So they were all caught by surprise as Jessie gave the trio a big group hug.

“That was amazing. Absolute defeat. And I couldn’t have done it without you~” Jessie’s happiness was sort of contagious, as the three Pokemon found themselves smiling for the first time. “Now eat your treats and rest up, tomorrow we have a long day of transformation ahead of us.”

With that, Jessie returned the Pokemon to their pokeballs, patting the balls with care as she thought about who else had wronged her in the past, so she could do the same to them. As she thought, Meowth approached her, a large grin on his face. 

“I gotta say Jessie, I’m impressed. I didn’t know what da boss’ plan wus gonna be, but I certainly didn’t expect this!” Jessie turned to face Meowth, a large confident smile on her face.

“Yes, well… Stealing Pokemon is great and all, but the boss found that prostitution is actually Team Rocket’s most lucrative business. And now that we can make… That” She said, pointing at Ashley while she ravaged James’ cock with her mouth. “We’re in for a lot of money.”

“Yeah! I really like this plan.” Meowth said, admiring Jessie’s work.

“So, do I Meowth.” She responded. “So, do I.”

**Author's Note:**

> Blam! A double whammy for ya face! I kinda had it ready before the previous one, so it's up now. This one's an anonymously requested story from someone on DA. It's been in planning for a while, so I'm glad it's finally done. This is also probably the last request I'm going to be doing for a bit, unless the request is REALLY good. Kinda want to work on my own stuff for a bit. As for the content, I had a lot of fun with this one. Haven't really worked with dressing and makeup much, but it was interesting. I also haven't done a lot of pure MtF tf, so this is kind of a breath of fresh air. I know that most of my stories are FtM, as I like it more than MtF, but honestly MtF is pretty good too! Anyways, hope you liked it!


End file.
